Rhodium- and iridium-catalyzed oxidative coupling of benzoic acids with alkynes and alkenes

References

1. (a) J. Tsuji. Palladium Reagents and Catalysts, 2nd ed., John Wiley, Chichester (2004);10.1002/0470021209Search in Google Scholar

1. (b) A. de Meijere, F. Diederich. Metal-Catalyzed Cross-Coupling Reactions, 2nd ed., Wiley-VCH, Weinheim (2004);10.1002/9783527619535Search in Google Scholar

1. (c) doi:10.1021/cr020007u, K. Fagnou, M. Lautens. Chem. Rev. 103, 169 (2003);Search in Google Scholar

1. (d) doi:10.1021/cr9903048, I. P. Beletskaya, A. V. Cheprakov. Chem. Rev. 100, 3009 (2000).Search in Google Scholar

2. (a) doi:10.1021/ar000209h, C. Jia, T. Kitamura, Y. Fujiwara. Acc. Chem. Res. 34, 633 (2001);Search in Google Scholar

2. (b) doi:10.1021/ja01053a047, Y. Fujiwara, I. Moritani, S. Danno, S. Teranishi. J. Am. Chem. Soc. 91, 7166 (1969).Search in Google Scholar

3. doi:10.1038/366529a0, S. Murai, F. Kakiuchi, S. Sekine, Y. Tanaka, A. Kamatani, M. Sonoda, N. Chatani. Nature 366, 529 (1993).Search in Google Scholar

4. (a) doi:10.1021/cr0509760, D. Alberico, M. E. Scott, M. Lautens. Chem. Rev. 107, 174 (2007);Search in Google Scholar

4. (b) doi:10.1246/cl.2007.200, T. Satoh, M. Miura. Chem. Lett. 36, 200 (2007);Search in Google Scholar

4. (c) T. Satoh, M. Miura. J. Synth. Org. Chem. 64, 1199 (2006);10.5059/yukigoseikyokaishi.64.1199Search in Google Scholar

4. (d) doi:10.1016/j.molcata.2006.02.035, B. L. Conley, W. J. Tenn III, K. J. H. Young, S. K. Ganesh, S. K. Meier, V. R. Ziatdinov, O. Mironov, J. Oxgaard, J. Gonzales, W. A. Goddard III, R. A. Periana. J. Mol. Catal. A 251, 8 (2006);Search in Google Scholar

4. (e) M. Miura, T. Satoh. In Handbook of C-H Transformations, G. Dyker (Ed.), Vol. 1, p. 223, Wiley-VCH, Weinheim (2005);Search in Google Scholar

4. (f) M. Miura, T. Satoh. Top. Organomet. Chem. 14, 55 (2005);10.1007/b104129Search in Google Scholar

4. (g) doi:10.1002/adsc.200303094, F. Kakiuchi, N. Chatani. Adv. Synth. Catal. 345, 1077 (2003);Search in Google Scholar

4. (h) doi:10.1002/1521-3765(20020603)8:11<2622::AID-CHEM2622>3.0.CO;2-#, C.-H. Jun, C. W. Moon, D.-Y. Lee. Chem.Eur. J. 8, 2622 (2002);Search in Google Scholar

4. (i) doi:10.1021/cr0104330, V. Ritleng, C. Sirlin, M. Pfeffer. Chem. Rev. 102, 1731 (2002);Search in Google Scholar

4. (j) M. Miura, M. Nomura. Top. Curr. Chem. 219, 211 (2002);10.1007/3-540-45313-X_6Search in Google Scholar

4. (k) doi:10.1021/ar960318p, F. Kakiuchi, S. Murai. Acc. Chem. Res. 35, 826 (2002);Search in Google Scholar

4. (l) doi:10.1002/(SICI)1521-3773(19990614)38:12<1698::AID-ANIE1698>3.0.CO;2-6, G. Dyker. Angew. Chem., Int. Ed. 38, 1698 (1999);Search in Google Scholar

4. (m) F. Kakiuchi, F. Murai. Top. Organomet. Chem. 3, 47 (1999);10.1007/3-540-68525-1_3Search in Google Scholar

4. (n) doi:10.1021/cr9411886, A. E. Shilov, G. B. Shul'pin. Chem. Rev. 97, 2879 (1997).Search in Google Scholar

5. (a) doi:10.1021/jo980584b, M. Miura, T. Tsuda, T. Satoh, S. Pivsa-Art, M. Nomura. J. Org. Chem. 63, 5211 (1998);Search in Google Scholar

5. (b) doi:10.1246/cl.1997.1103, M. Miura, T. Tsuda, T. Satoh, M. Nomura. Chem. Lett. 1103 (1997).Search in Google Scholar

6. (a) doi:10.1002/adsc.200600389, C. Amatore, C. Cammoun, A. Jutand. Adv. Synth. Catal. 349, 292 (2007);Search in Google Scholar

6. (b) doi:10.1021/ja0176907, M. D. K. Boele, G. P. F. van Strijdonck, A. H. M. de Vries, P. C. J. Kamer, J. G. de Vries, P. W. N. M. van Leeuwen. J. Am. Chem. Soc. 124, 1586 (2002).Search in Google Scholar

7. doi:10.1039/b417035k, E. Capito, J. M. Brown, A. Ricci. Chem. Commun. 1854 (2005).Search in Google Scholar

8. G. Cai, Y. Fu, Y. Li, X. Wan, Z. Shi. J. Am. Chem. Soc. 129, 7666 (2007).Search in Google Scholar

9. (a) doi:10.1021/ja068993+, L. J. Goossen, N. Rodriguez, B. Melzer, C. Linder, G. Deng, L. M. Levy. J. Am. Chem. Soc. 129, 4824 (2007);Search in Google Scholar

9. (b) doi:10.1021/ol070495y, J.-M. Becht, C. Catala, C. Le Drian, A. Wagner. Org. Lett. 9, 1781 (2007);Search in Google Scholar

9. (c) doi:10.1126/science.1128684, L. J. Goossen, G. Deng, L. M. Levy. Science 313, 662 (2006);Search in Google Scholar

9. (d) doi:10.1021/ja063511f, P. Forgione, M.-C. Brochu, M. St-Onge, K. H. Thesen, M. D. Bailey, F. Bilodeau. J. Am. Chem. Soc. 128, 11350 (2006);Search in Google Scholar

9. (e) doi:10.1021/ja0259279, T. Okazawa, T. Satoh, M. Miura, M. Nomura. J. Am. Chem. Soc. 124, 5286 (2002);Search in Google Scholar

9. (f) doi:10.1021/ja071845e, H. A. Chiong, Q.-N. Pham, O. Daugulis. J. Am. Chem. Soc. 129, 9879 (2007);Search in Google Scholar

9. (g) doi:10.1021/ja0701614, R. Giri, N. Maugel, J.-J. Li, D.-H. Wang, S. P. Breazzano, L. B. Saunders, J.-Q. Yu. J. Am. Chem. Soc. 129, 3510 (2007).Search in Google Scholar

10. (a) doi:10.1016/S0040-4020(03)00212-6, R. Rossi, A. Carpita, F. Bellina, P. Stabile, L. Mannina. Tetrahedron 59, 2067 (2003);Search in Google Scholar

10. (b) doi:10.1021/jo034308v, T. Yao, R. C. Larock. J. Org. Chem. 68, 5936 (2003);Search in Google Scholar

10. (c) R. S. Mali, K. N. Babu. J. Org. Chem. 63, 2488 (1998) and refs. cited therein.10.1021/jo971622eSearch in Google Scholar PubMed

11. (a) doi:10.1016/j.tetlet.2005.12.104, J. M. Lee, S. Chang. Tetrahedron Lett. 47, 1375 (2006);Search in Google Scholar

11. (b) doi:10.1021/ja016280f, B. D. Dangel, J. A. Johnson, D. Sames. J. Am. Chem. Soc. 123, 8149 (2001).Search in Google Scholar

12. (a) doi:10.1055/s-2006-942504, H. B. Mereyala, G. Pathuri. Synthesis 2944 (2006);Search in Google Scholar

12. (b) doi:10.1021/jo050440e, V. Subramanian, V. Rao Batchu, D. Barange, M. Pal. J. Org. Chem. 70, 4778 (2005);Search in Google Scholar

12. (c) doi:10.1016/j.tetlet.2004.04.110, X. Wu, A. K. Mahalingam, Y. Wan, M. Alterman. Tetrahedron Lett. 45, 4635 (2004);Search in Google Scholar

12. (d) doi:10.1246/bcsj.74.1437, Y. Lee, Y. Fujiwara, K. Ujita, M. Nagamoto, H. Ohta, I. Shimizu. Bull. Chem. Soc. Jpn. 74, 1437 (2001);Search in Google Scholar

12. (e) doi:10.1021/jo9821628, R. C. Larock, M. J. Doty, X. Han. J. Org. Chem. 64, 8770 (1999);Search in Google Scholar

12. (f) doi:10.1021/jo982451w, K. Orito, M. Miyazawa, R. Kanbayashi, M. Tokuda, H. Suginome. J. Org. Chem. 64, 6583 (1999);Search in Google Scholar

12. (g) doi:10.1021/jo00117a023, H.-Y. Liao, C.-H. Cheng. J. Org. Chem. 60, 3711 (1995);Search in Google Scholar

12. (h) doi:10.1021/jo00116a003, R. C. Larock, E. K. Yum, M. J. Doty, K. K. C. Sham. J. Org. Chem. 60, 3270 (1995).Search in Google Scholar

13. S. S. Stahl. Angew. Chem., Int. Ed. 43, 3400 (2004) and refs. therein.10.1002/anie.200300630Search in Google Scholar PubMed

14. (a) doi:10.1016/j.tetlet.2005.09.179, T. Sugihara, T. Satoh, M. Miura. Tetrahedron Lett. 46, 8269 (2005);Search in Google Scholar

14. (b) doi:10.1002/adsc.200404145, T. Sugihara, T. Satoh, M. Miura, M. Nomura. Adv. Synth. Catal. 346, 1765 (2004);Search in Google Scholar

14. (c) doi:10.1002/anie.200351905, T. Sugihara, T. Satoh, M. Miura, M. Nomura. Angew. Chem., Int. Ed. 42, 4672 (2003);Search in Google Scholar

14. (d) doi:10.1021/ja0280269, T. Yasukawa, T. Satoh, M. Miura, M. Nomura. J. Am. Chem. Soc. 124, 12680 (2002);Search in Google Scholar

14. (e) doi:10.1016/S0022-328X(01)01439-5, K. Oguma, M. Miura, T. Satoh, M. Nomura. J. Organomet. Chem. 648, 297 (2002);Search in Google Scholar

14. (f) doi:10.1016/S0040-4039(00)00238-0, Y. Kametani, T. Satoh, M. Miura, M. Nomura. Tetrahedron Lett. 41, 2655 (2000);Search in Google Scholar

14. (g) doi:10.1021/jo960915p, K. Kokubo, K. Matsumasa, M. Miura, M. Nomura. J. Org. Chem. 61, 6941 (1996);Search in Google Scholar

14. (h) doi:10.1021/om00010a016, K. Kokubo, M. Miura, M. Nomura. Organometallics 14, 4521 (1995).Search in Google Scholar

15. (a) doi:10.1006/jcat.2001.3471, T. Matsumoto, R. A. Periana, D. J. Taube, H. Yoshida. J. Catal. 206, 272 (2002);Search in Google Scholar

15. (b) doi:10.1246/cl.2000.1064, T. Matsumoto, H. Yoshida. Chem. Lett. 1064 (2000).Search in Google Scholar

16. (a) doi:10.1039/c39920001334, A. K. Fazlur-Rahman, J.-C. Tsai, K. M. Nicholas. J. Chem. Soc., Chem. Commun. 1334 (1992);Search in Google Scholar

16. (b) doi:10.1016/S0020-1693(00)80808-7, M. Bressan, A. Morvillo. Inorg. Chim. Acta 166, 177 (1989);Search in Google Scholar

16. (c) doi:10.1002/anie.198207341, H. Mimoun. Angew. Chem., Int. Ed. Engl. 21, 734 (1982);Search in Google Scholar

16. (d) doi:10.1021/ja00485a031, H. Mimoun, M. M. Perez-Machirant, I. Seree de Roch. J. Am. Chem. Soc. 100, 5437 (1978).Search in Google Scholar

17. (a) doi:10.1021/ja00722a015, G. M. Whitesides, W. J. Ehmann. J. Am. Chem. Soc. 92, 5625 (1970);Search in Google Scholar

17. (b) doi:10.1021/ja01532a024, W. Herwig, W. Metlesics, H. Zeiss. J. Am. Chem. Soc. 81, 6203 (1959);Search in Google Scholar

17. (c) doi:10.1021/jo0346656, S. Kawasaki, T. Satoh, M. Miura, M. Nomura. J. Org. Chem. 68, 6836 (2003);Search in Google Scholar

17. (d) doi:10.1021/om00152a019, G. Wu, A. L. Rheingold, S. L. Feib, R. F. Heck. Organometallics 6, 1941 (1987);Search in Google Scholar

17. (e) doi:10.1246/cl.1986.797, T. Sakakibara, Y. Tanaka, T.-I. Yamasaki. Chem. Lett. 797 (1986);Search in Google Scholar

17. (f) doi:10.1021/ol049176m, W. Huang, X. Zhou, K.-I. Kanno, T. Takahashi. Org. Lett. 6, 2429 (2004).Search in Google Scholar

18. (a) doi:10.1021/jo070735n, K. Ueura, T. Satoh, M. Miura. J. Org. Chem. 72, 5362 (2007);Search in Google Scholar

18. (b) doi:10.1021/ol070406h, K. Ueura, T. Satoh, M. Miura. Org. Lett. 9, 1407 (2007).Search in Google Scholar

19. doi:10.1039/dt9870002459, J. M. Kisenyi, G. J. Sunley, J. A. Cabeza, A. J. Smith, H. Adams, N. J. Salt, P. M. Maitlis. J. Chem. Soc., Dalton Trans. 2459 (1987).Search in Google Scholar